#1 The Undertaker (1990s, 2000s, 2010s, 2020s)
A name that’s synonymous with WWE, The Undertaker joined the company in November 1990 as Kane the Undertaker. His gimmick saw him portray a character who was impervious to pain.
As time went by, The Undertaker became one of the most followed and loved wrestlers in WWE. Undertaker’s character and gimmick allowed WWE to come up with unique matches such as Buried Alive matches and Casket matches. Over time, he became known as The Deadman, The Phenom, the motorcycle-riding American Bad A**, and Big Evil.
Each and every gimmick worked with the Superstar, as he was a crowd favorite no matter what character he was playing. Throughout his WWE career, he won 7 World Championships and held the Tag Team Championship on multiple occasions.
However, The Phenom was much bigger than the championships he held, and the company realized that and built him as a completely different Superstar. Defeating The Undertaker was an achievement by itself, and his WrestleMania undefeated streak (he eventually lost and sits at 22-2) remains one of the most iconic achievements in wrestling history.
The Undertaker only works a few matches a year now, and usually appears for big events such as Crown Jewel and WrestleMania. He has missed only 2 WrestleMania events since his first in 1991 - WrestleMania 2000 due to an injury, and this year's WrestleMania 35, as he has taken a much lighter schedule and was not asked to be a part of the event.
2020 will mark his 30th year in the company, and we’re sure that he will take to the ring once again to celebrate the milestone, and maybe even compete in his final WrestleMania match.